Boron tribromide → HCID 178512016, compound

HRID 30437Notes

Reaction equation

HRID 30437 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21]C)[CH:17]=3)[CH:12]=2)=[NH:10])=[CH:4][CH:3]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=3)[CH:12]=2)=[NH:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178487483HCID 178487483, compound

Product 1

HCID 178512016HCID 178512016, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.104 g (0.33 mmol) of N-(4-chloro-phenyl)-6-methoxy -naphthalene-2-carboxamidine in 5 mL of dichloromethane was added 1.5 mL (1 M, 1.5 mmol) of BBr3 in dichloromethane at 0° C. It was warmed to room temperature overnight, poured into 125 mL of saturated NaHCO3 and extracted with three 50 mL portions of ethyl acetate. The combined organic extracts were washed with 125 mL of brine, dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC eluting with 50% ethyl acetate in hexanes plus 1% NH4OH to give 0.014 g of N-(4-chloro-phenyl)-6-hydroxy-naphthalene-2-carboxamidine.

Workup

  1. extractionextracted with three 50 mL portions of ethyl acetate
  2. washThe combined organic extracts were washed with 125 mL of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. washeluting with 50% ethyl acetate in hexanes plus 1% NH4OH

Sources & evidence

ORD record
ord-2e02cd8b9669442e8c968f5ad9a9c68d
Source dataset
uspto-grants-2008_09
Patent number
US07423149B2

Reaction notes

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